For this trophy you must do three playthroughs with the Hillbilly as you must use all 7 characters at the carnival (The hillbilly challenge area).
When at the carnival, after activating the Fortune teller with the fuse box, have each of your characters speak with the fortune teller box. Use a different two characters each playthrough to minimize time spent.
i.e. (Hillbilly, Twins, Adventurer/ Hillbilly, Knight, monk/ Hillbilly, Scientist, Time Traveller)
Unfortunately, you do have to then complete the playthrough for it to count.
This must be done BEFORE using the wheel of misfortune as it will then be unusable.